Synthesis of New 5- or 7-Substituted 3-Nitroimidazo[1,2-a]pyridine Derivatives Using SNAr and Palladium-Catalyzed Reactions To Explore Antiparasitic Structure–Activity Relationships - Aix-Marseille Université Access content directly
Journal Articles Synthesis: Journal of Synthetic Organic Chemistry Year : 2023

Synthesis of New 5- or 7-Substituted 3-Nitroimidazo[1,2-a]pyridine Derivatives Using SNAr and Palladium-Catalyzed Reactions To Explore Antiparasitic Structure–Activity Relationships

Abstract

To study the antikinetoplastid structure–activity relationships in a 3-nitroimidazo[1,2-a]pyridine series, we explored the substitution of positions 5 and 7 of the scaffold, developing nucleophilic aromatic substitution reactions and palladium-catalyzed Suzuki–Miyaura, Sonogashira, and Buchwald–Hartwig cross-coupling reactions that had never been reported at these positions in this series. In four steps from 2-amino(bromo)pyridines, 33 original compounds were obtained, allowing a better definition of the antiparasitic pharmacophore.
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Wednesday, June 19, 2024
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Wednesday, June 19, 2024
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hal-04534726 , version 1 (05-04-2024)

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Romain Paoli-Lombardo, Nicolas Primas, Sandra Bourgeade-Delmas, Alix Sournia-Saquet, Caroline Castera-Ducros, et al.. Synthesis of New 5- or 7-Substituted 3-Nitroimidazo[1,2-a]pyridine Derivatives Using SNAr and Palladium-Catalyzed Reactions To Explore Antiparasitic Structure–Activity Relationships. Synthesis: Journal of Synthetic Organic Chemistry, 2023, 56 (08), pp.1297-1308. ⟨10.1055/a-2232-8113⟩. ⟨hal-04534726⟩
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